trans-1-nitro-2-phenylcyclopropane | 15267-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-1-nitro-2-phenylcyclopropane
• 英文别名: trans-(2-nitrocyclopropyl)benzene；[(1R,2S)-2-nitrocyclopropyl]benzene
• CAS: 15267-27-3
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: XRNLPUUQLOMTGY-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-1-nitro-2-phenylcyclopropane 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以78%的产率得到5-phenyl-3-isoxazolidinone
  参考文献：
  名称：

  Factors in Molecular Structure to Activate Nitro Compounds for Organic Transformations

  摘要：

  Activation of nitro compounds was accomplished by introduction of angle strain, gamma,delta-unsaturation, or a gamma-silyl group. Results from a systematic study indicate that coexistence of two or more of these factors in aliphatic nitro compounds allowed transformations to take place under ambient conditions upon catalysis with AlCl3, TiCl4, BF3. OEt2. Or SnCl4. Consequently, structurally modified nitro starting materials led to products in the class of nitroalkyl cyclopentadiene, cyclohydroxamic ester, and chlorohydroxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00008-9
• 作为产物：
  描述：

  ethyl 1-nitro-cis-2-phenylcyclopropanecarboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 trans-1-nitro-2-phenylcyclopropane
  参考文献：
  名称：

  Decarboxylation of sodium 1-nitrocyclopropanecarboxylates. A facile synthesis of nitrocyclopropanes

  摘要：

  DOI：

  10.1021/jo00288a063

文献信息

• An Expedient and Practical Method for the Synthesis of a Diverse Series of Cyclopropane α-Amino Acids and Amines
  作者：Ryan P. Wurz、André B. Charette

  DOI：10.1021/jo035596y

  日期：2004.2.1

  described. Nitrocyclopropane carboxylates can be readily prepared through treatment of α-nitroesters and iodobenzene diacetate or α-nitro-α-diazoesters with a Rh(II) catalyst and an olefin. Reduction of the nitro group using zinc/HCl in i-PrOH affords substituted cyclopropane α-amino esters in modest to high yields (54−99%). A “one-pot” procedure involving sequential cyclopropanation and reduction is described

  描述了用于制备多种系列的环丙烷α-氨基酸的实用合成方法。硝基环丙烷羧酸盐可以通过用Rh（II）催化剂和烯烃处理α-硝基酯和碘代苯二乙酸酯或α-硝基-α-重氮酸酯来轻松制备。在i -PrOH中使用锌/ HCl还原硝基基团可中等至高收率（54-99％）提供取代的环丙烷α-氨基酯。描述了涉及顺序环丙烷化和还原的“一锅法”程序。该方法也可用于制备芳基环丙胺（三个实例）。
• Nitrocyclopropanes from nitrodiazomethanes. Preparation and reactivity
  作者：P.E. O'Bannon、William P. Dailey

  DOI：10.1016/s0040-4020(01)89052-9

  日期：——

  Nitrodiazo compounds cyclopropanate electron rich alkenes in the presence of rhodium(II) acetate. The yields and diastereoselectivities are dependent on both the alkene and the nitrodiazo precursor. Nitrocyclopropanecarboxylates undergo ring opening, reduction and hydrolysis.

  硝基重氮化合物在乙酸铑（II）的存在下形成环丙酸酯富电子的烯烃。产率和非对映选择性同时取决于烯烃和硝基二偶氮前体。硝基环丙烷羧酸酯经历开环，还原和水解作用。
• Cyclopropanation of Olefins with Nitromethane
  作者：Tore Hansen、Hanne Bonge

  DOI：10.1055/s-2006-958437

  日期：2007.1

  A procedure for the use ofnitromethane as an iodonium ylide precursor has been developed. Electron-rich olefins are cyclo-propanated with nitromethane in the presence ofbis(acetoxy)iodobenzene, a base and a Rh(II) catalyst to provide nitrocyclopropanes in moderate to good yields.

  已开发出使用硝基甲烷作为碘鎓叶立德前体的程序。在双（乙酰氧基）碘苯、碱和 Rh(II) 催化剂存在下，富电子烯烃与硝基甲烷环丙烷化，以中等至良好的产率提供硝基环丙烷。
• Copper(I) Photocatalyzed Bromonitroalkylation of Olefins: Evidence for Highly Efficient Inner‐Sphere Pathways
  作者：Alexander Reichle、Magdalena Koch、Hannes Sterzel、Lea‐Joy Großkopf、Johannes Floss、Julia Rehbein、Oliver Reiser

  DOI：10.1002/anie.202219086

  日期：——

  Photocatalytic bromonitroalkylations of activated and unactivated olefins with broad scope become possible in the presence of CuI-photocatalysts. The key to success for this transformation is the highly efficient interaction of CuII with radical intermediates, which can even outperform a highly favorable cyclization of a transient to a persistent radical.

  在 Cu I -光催化剂存在下，具有广泛范围的活化和未活化烯烃的光催化溴硝基烷基化成为可能。这种转化成功的关键是 Cu II与自由基中间体的高效相互作用，它甚至可以胜过从瞬态自由基到持久自由基的高度有利的环化。
• Photocatalytic intermolecular bromonitroalkylation of styrenes: synthesis of cyclopropylamine derivatives and their evaluation as LSD1 inhibitors
  作者：Darong Kim、Hui-Jeon Jeon、Yoonna Kwak、Sun Joo Lee、Tae-Gyu Nam、Ji Hoon Yu、Hongchan An、Ki Bum Hong

  DOI：10.1039/d3ra07830b

  日期：——

  serves as a source of both nitroalkyl and bromine for direct and regioselective formation of C-Br and C-C bonds from alkenes, and additional cyclization provides C-C bonds to the cyclopropylamine core as an LSD1 inhibitor.

  本文描述了一种温和且有效的烯烃光氧化还原催化溴硝基烷基化方法。在此反应中，溴硝基甲烷作为硝基烷基和溴的来源，用于从烯烃直接和区域选择性地形成 C-Br 和 CC 键，并且额外的环化为作为 LSD1 抑制剂的环丙胺核心提供 CC 键。